Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides

a technology of pyrimidin and derivatives, which is applied in the field of 3alkyl-5fluoro4imino3, 4dihydropyrimidin2 (1h) one compounds, can solve the problem that no single fungicide is useful in all situations, and achieves the effects of less cost, improved performance and convenient us

Active Publication Date: 2015-12-17
ADAMA MAKHTESHIM LTD
View PDF4 Cites 18 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patent is about a new type of fungicide that can protect plants from damage caused by different types of fungi. The new fungicide is made from a specific compound that has better performance and is easier to use than other fungicides. The patent also describes a composition that can be used to protect plants from attack by various types of fungi and to treat plants that are already infested by them.

Problems solved by technology

Generally, no single fungicide is useful in all situations.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides
  • 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides
  • 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of (E)-5-fluoro-1-((4-methoxyphenyl)sulfonyl)-3-methyl-4-(methylimino)-3,4-dihydropyrimidin-2(1H)-one (F1)

[0093]

[0094]5-fluoro-4-imino-1-((4-methoxyphenyl)sulfonyl)-3,4-dihydropyrimidin-2(1H)-one (1.8 g, 6.01 mmol, prepared as described in WO 2011 / 017547) was stirred at room temperature in dimethylformamide (DMF, 10 mL) under a blanket of nitrogen. Anhydrous potassium carbonate (K2CO3, 1.662 g, 12.03 mmol), and iodomethane (0.562 mL, 9.02 mmol) were added. The reaction mixture was stirred at ambient temperature for 3 days (d), poured onto ice water, and extracted with ethyl acetate (EtOAc, 4×50 mL). The combined organic fractions were washed with saturated NaCl solution (100 mL), dried over anhydrous magnesium sulfate (MgSO4), filtered and evaporated to yield the crude product mixture as a yellow solid (2 g). The crude mixture was purified by silica gel chromatography using a 0-100% EtOAc / hexanes gradient to provide the title compound as a white solid (0.16 g, 8.1%). Cha...

example 2

Preparation of N-(5-fluoro-1-((4-methoxyphenyl)sulfonyl)-2-oxo-2,3-dihydropyrimidin-4(1H)-ylidene)acetamide

[0095]

[0096]A dry 100 ml, round bottom flask equipped with magnetic stirrer and nitrogen inlet was charged with 4-amino-5-fluoro-1-((4-methoxyphenyl)sulfonyl)pyrimidin-2(1H)-one (1.0 g, 3.34 mmol) and 50 mL of anhydrous acetonitrile (CH3CN). To this solution was added anhydrous pyridine (0.27 mL, 3.34 mmol) followed by acetic anhydride (0.35 mL, 3.68 mmol). The reaction was stirred at ambient temperature for 17 hours (h). The reaction mixture was concentrated and the residue was chromatographed by silica gel flash chromatography eluting with a gradient of 100% hexane to 100% ethyl acetate (EtOAc). The pure fractions were combined and concentrated under vacuum on a rotary evaporator to afford N-(5-fluoro-1-((4-methoxyphenyl)sulfonyl)-2-oxo-2,3-dihydropyrimidin-4(1H)-ylidene)acetamide as a white solid (770 mg, 67.5%): 1H NMR (400 MHz, DMSO-d6) δ 10.82 (s, 1H), 8.61 (d, J=6.1 Hz, ...

example 3

Preparation of N-(5-fluoro-1-((4-methoxyphenyl)sulfonyl)-3-methyl-2-oxo-2,3-dihydropyrimidin-4(1H)-ylidene)acetamide (F31)

[0097]

[0098]A dry 50 mL round bottom flask equipped with magnetic stirrer and nitrogen inlet was charged with N-(5-fluoro-1-((4-methoxyphenyl)sulfonyl)-2-oxo-2,3-dihydropyrimidin-4(1H)-ylidene)acetamide (0.5 g, 1.465 mmol) and 10 mL of anhydrous N,N-dimethyl formamide (DMF). To this solution was added powdered lithium carbonate (216 mg, 2.93 mmol) followed by iodomethane (182 μL, 2.93 mmol). The reaction was stirred at ambient temperature for 12 hours. Additional lithium carbonate (108 mg, 1.465 mmoles) and iodomethane (91 μL, 1.465 mmoles) were added, and the reaction was stirred at ambient temperature for another two hours. The reaction mixture was poured into 50 mL of dichloromethane (CH2Cl2, DCM), and washed with 20 mL of water and 20 mL of saturated aqueous sodium chloride solution. The organic extract was dried over anhydrous magnesium sulfate (MgSO4), filt...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
particle sizeaaaaaaaaaa
temperatureaaaaaaaaaa
temperatureaaaaaaaaaa
Login to View More

Abstract

This present disclosure is related to the field of 3-alkyl-5-fluoro-4-substituted-imino-3,4-5 dihydropyrimidin-2(1H)-ones and their derivatives and to the use of these compounds as fungicides. Also provided are methods of controlling a fungal disease such as Septoria tritici, comprising administering an effective amount of the fungicide compound to at lease one surface associated with the plant, seed or soil.

Description

CROSS REFERENCE TO RELATED APPLICATIONS[0001]This application claims the benefit of U.S. Provisional Patent Application Ser. No. 61 / 747,683 filed Dec. 31, 2012, which is expressly incorporated by reference herein.BACKGROUND AND SUMMARY OF THE INVENTION[0002]Fungicides are compounds, of natural or synthetic origin, which act to protect and / or cure plants against damage caused by agriculturally relevant fungi. Generally, no single fungicide is useful in all situations. Consequently, research is ongoing to produce fungicides that may have better performance, are easier to use, and cost less.[0003]The present disclosure relates to 3-alkyl-5-fluoro-4-imino-3,4-dihydropyrimidin-2(1H)one compounds and their use as fungicides. The compounds of the present disclosure may offer protection against ascomycetes, basidiomycetes, deuteromycetes and oomycetes.[0004]One embodiment of the present disclosure may include compounds of Formula I:wherein R1 is:[0005]C1-C6 alkyl optionally substituted with...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(United States)
IPC IPC(8): A01N47/40A01N43/54C07D409/12A01N47/02A01N47/18C07D413/12A01N43/80C07D417/12A01N43/78C07D239/47A01N43/56
CPCA01N47/40C07D239/47A01N43/54C07D409/12A01N47/02A01N47/18C07D413/12A01N43/80C07D417/12A01N43/78A01N43/56A01N47/12C07D403/12A01N47/22A61K31/513C07B59/002C07B2200/05
Inventor LORSBACH, BETHROSS, RONALDOWEN, W. JOHNWEBSTER, JEFFERY D.STELZER, LINDSAYYAO, CHENGLINLEPLAE, JR., PAUL R.GALLIFORD, CHRIS V.
Owner ADAMA MAKHTESHIM LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com